Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction,The Journal of Organic Chemistry

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Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-11-09 , DOI: 10.1021/acs.joc.0c01926
Yuki Yamamoto ₁ , Shin-ichi Kawaguchi ₂ , Misaki Nishimura ₁ , Yuki Sato ₁ , Yoshihisa Shimada ₁ , Akihiro Tabuchi ₁ , Akihiro Nomoto ₁ , Akiya Ogawa ₁

Affiliation

This study shows that phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity. The concomitantly formed fluorous phosphine oxide was extracted from the reaction mixture using a fluorous biphasic system. The fluorous phosphine was regenerated by reducing the fluorous phosphine oxide with diisobutylaluminum hydride. Finally, a series of gram scale phosphorus recycling processes were performed, which included the Wittig reaction, separation, reduction, and reuse.

中文翻译：

磷循环维蒂希反应：氟膦的设计，简便合成及其在维蒂希反应中的可重复利用过程

这项研究表明，可以在Wittig反应中使用适当的氟膦来回收磷源。由空气稳定的膦试剂合成了设计的氟膦，该磷膦在其磷原子和全氟烷基之间具有一个乙烯间隔基。合成的膦可用于Wittig反应过程，以足够的收率和立体选择性获得各种烯烃。使用氟双相体系从反应混合物中提取伴随形成的氟氧化膦。通过用二异丁基氢化铝还原氟代膦氧化物来再生氟代膦。最后，进行了一系列的克级磷回收过程，包括Wittig反应，分离，还原和再利用。

更新日期：2020-11-21

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